Sep 12

Going to post some books this week

For a variety of reasons, I haven’t been posting much about what (little) I’ve been reading this year, but am going to try to catch up this year, so will have a few book posts in a row…

Jun 12


Yesterday, Kathy & I brought home our new baby boy, ZBL. He was born on Tuesday at Stanford Hospital — he and Kathy are both doing super well, and SPL is excited to be a big brother.

What I wanted to write about this morning is optimism. The act of bringing home a new baby is such an incredible act of optimism. It’s just impossible not to look at everything with new eyes and to see potential everywhere.

As I get to know Z, I find that just talking to him, telling him about all the things that he’ll learn about and interact with and make — it fills me with a spirit of possibility.

Raising kids is challenging, no doubt about it. And there are days which can be pretty long.

But we get so many things from our kids, and like it did with his big brother, it’s amazing to me how much Z coming into the world has already given me, how much it’s broadened my perspective, and how he’s already helping me see so much optimism and possibility in the world.

Apr 12


N.B.: this post might be in the “too much information” category for some of you. If so, just click on to the next thing.

I’ve been meaning to write this post for months, but haven’t been able to get it done. Partly because it’s been such a busy year, but partly too because I’m not really sure what to say.

Nonetheless, I think it’s important to write, so here goes.

Kathy & I are expecting our second child in June — we’re so, so excited about it. We had our first child nearly 7 years ago — and he’s the sun and the moon for both of us — he’s everything, really. Despite the fact that Kathy & I have known each other since high school in 1985 (no joke!) and have been married since 2000, we waited relatively late to start our family, having SPL when we were each 35. Lots of reasons for that, but I think ultimately we wanted to be “just us” as a married couple for a while, get that sorta figured out a little bit.

It didn’t happen right away for us — it took a couple of years of trying for it to happen. At some level, that was the first really clear indication in our lives that there are some things that you just can’t schedule, you can’t control, don’t always happen the way you draw them up.

Nonetheless, we waited a couple of years to start thinking about our second child — and it was a considerably harder path than the first time around. We went through several surgeries, IUI cycles, and several cycles of IVF. We never really figured out exactly what the problems were, just factors that might have made things less likely.

We started at Stanford, and after a bunch of research and talking with friends we could find, we ended up going to a clinic in Denver. We went through a bunch of invasive & emotional & tiring procedures in Denver that required Kathy to be away from SPL & me for a week or two at a time. My mom came out several times to help — not sure what we would have done without her.

And then, in the cycle that we had decided would be our last time, everything worked. That was about 7 months ago now, and our second child appears to be healthy & heading towards coming into the world in June. We’ll both be 41, and SPL will be nearly 7. So we’re excited, and a little terrified, too (but in mostly a good way).

But here’s why I wanted to write this: as we went on our own path, we would often tentatively mention a word or a phrase related to IVF and when we saw the person we were with nod or respond, then we would discuss a little more actively. We’re so grateful for our friends along the way who had gone before us — they were all incredibly supportive and helpful.

I figure there must be many, many more people going through this than we know. Especially here in California I think people are waiting longer and longer to have kids — so you’d expect more problems along the way.

But there’s a reluctance, or embarrassment, or something that keeps people from talking about it much. I hope that that goes away over time as it becomes more common and better understood.

That’s why I wanted to write this, ultimately — not because I have a ton to add to the conversation — I have some modest insight from our own experience, but mostly it’s been a very personal journey for Kathy & me. But I hope by writing that more people will start to feel that it’s okay to talk about, to write about.

Like so many other areas, sunshine and knowledge are hugely powerful. We’ve been lucky to have so many friends in this along the way, and I hope others going through it do also.

Looking forward to June. 🙂

Mar 12


At TED, I’ve found there are overall themes of each conference that speakers keep coming to again & again — often not the official theme, but a reflection of where the mood of the community is. And then I’ve found that wherever I am personally, I get coherence in different ways. For me this year, and for many of the folks I’ve talked with, the theme is intentionality: how to figure out and live a life that you want to live, instead of taking the one that comes to you.

As a friend said last night, it feels like there were maybe a half dozen talks about just this thing. From Sherry Turkle’s worry about how devices are making us alone, together; to Jen Pahlka’s excellent thoughts on becoming better and more involved citizens; to David Kelly’s thoughts on creative confidence and how to nurture it; and to Bryan Stevenson’s unbelievable talk about how he’s made a difference, and the people in his life who have helped him “keep his eyes on the prize.”

I’m coming to view intentionality, depth of thought and connection, and the power to focus as the central developmental challenges of our society today. We’re going through an incredibly rapid transformation into an always connected, real-time, perma-entertained, ever stimulated world — and it’s becoming clear to me that, somewhat ironically, it’s the people who can take advantage of all of that, while also ultimately staying within themselves, will be the ones who make the most profound and positive changes in our world.

So that applies to all of us, and implies much about how to think about living our lives, interacting with each other, and teaching our children.

I’ve been thinking a lot over the last few months — or really probably the last year or so — about how to be more intentional in my life — i think this week has catalyzed some of my thinking, so I’ll plan to write about a bunch of different aspects of it as I work through my own re-intentioning of my life.

Jan 12

Tips for Entrepreneurs from a First Year VC

[Cross posting this (with better image!) from PandoDaily where I published this as a guest post.]

A close friend of mine likes to joke about how entrepreneurs & operators who become venture capitalists are “trading in their blue light sabers for red ones” – it’s a funny analogy…naturally, comparing investors to Sith Lords seems to fit pretty well some days.

But the benefit of switching from one side to the other is that perspective can sometimes be illuminated. After nearly 20 years of operating at places like Mozilla, Reactivity, Trilogy & Apple, I still tend to think like an entrepreneur myself, so some of the assumptions of life inside a VC are maybe a little more obvious to me than folks who have been around longer.

So here are some observations about my first year of VC life, and then some of the ways that being on the “inside” has changed the way I think that entrepreneurs should think about approaching investors – things I wish I had understood myself when I was pitching.

A Year of Observations about VC Life 

Life as a VC is a sea of meetings. Really, it is a lot of meetings. Most of them are single meetings, with no follow-ups. Most don’t result in an investment in a company at all. In 2011 I had first meetings with just over 350 companies, plus another 100 more as parts of business plan judging and demo days. Those meetings resulted in just four investments for me (Tumblr, Dropbox, Clearslide and Citrus Lane) plus a handful of seed investments.

That’s a massive “bias-to-no” for any profession – 99% or so. It’s a tough negative bias, and every investor I know is affected by it in some way. But that one percent is like a lightning strike: those meetings can form the basis for some of the most interesting and meaningful work you’ll ever do.

High fidelity communication is impossible. Because so many meetings are one-offs like I described, it’s very hard to communicate effectively. As an operator, you get good at being direct with the people you work with – or you fail.

In the context of a startup, relationships are developed over a period of months or years, so that candor can be better understood and more nuanced, resulting in communications that are efficient and effective, without hurt feelings from misunderstandings.

Venture meetings aren’t like that. They’re incredibly overloaded: you’re trying to have a really good communication about who you are, what you’ve built, and how you want to grow. And you’re trying to do it in what is very often an extremely emotionally significant context of someone putting everything at risk to change the world. All with no existing relationship context to fall back on.

As an investor, I feel that a situation like that deserves my fullest possible attention, and my best questions about and suggestions for the business. But since we’ve never interacted before, there’s the danger of seeming too harsh in cases like that – we don’t have the shared context, vocabulary and trust frameworks in place that you do in longer term relationships. I think that’s why so many investors are often vague or non-responsive in their interactions afterwards – something I’ve tried very hard to avoid, although with imperfect success so far.

Timing is everything, and everyone is multi-tasking. This applies to both the startup and the investor I’ve found – because each has their own set of work going, and any number of competing projects and priorities. The right thing coming by at the wrong time can be as challenging as an investment that just isn’t a natural fit. Life as a VC has different patterns and rhythms than life for operators – the nature of VC work is that you’ve got multiple companies and entrepreneurs you’re working with all the time, plus a constant stream of new folks to meet, and often in wildly different domains.

This means constant context switching, and there are times when excellent entrepreneurs and startups come through when it’s just hard or impossible to take focus from existing or in process investments. That creates a severe asymmetry: as an entrepreneur, you’re thinking about one thing (broadly defined as your startup), deeply,all the time, while investors that you’re talking with are trying to juggle many at once.

Venture firms and partners are idiosyncratic and highly personal. When I raised money for my own startup, I didn’t know much about how to think about approaching VCs. I knew folks at various firms, and mostly went to talk with those who I knew and then went through their process over the subsequent several weeks. I figured that VCs were all mostly similar to each other.

I’ll say candidly that in my case, I was extremely lucky when that “strategy” worked – my investors were Mitch Kapor and Peter Fenton when they were both at Accel Partners – they were incredibly great for us, and I’ve had fantastically productive relationships with both for more than a decade now. But at some level it was really just dumb luck. I could easily have found a firm and partners who wouldn’t have worked.

Every firm has different culture: some are collaborative, others more solo practices; a small few (including Greylock) consist of former or current entrepreneurs, other firms consist of people who have been investors most of their careers; some are progressive, some are conservative. And even in partnerships, everyone there is different. Different in interests, skills, capabilities, stage in life, and temperament, at the very least.

But here’s the thing: meeting with an amazing entrepreneur can change your whole year. 

That’s why you do it. To find people to change the world with. I’ve been very lucky this year to work with some incredible entrepreneurs and teams, not just limited to the companies we were able to invest in. And that’s what we’re all looking for: not just the opportunity to make great investments, but the chance to work with people who are setting out to make the world the way they want it. There’s no more optimistic and hopeful endeavor, and it’s 100% addictive.

Suggestions on Interacting with VCs

Given that context on what it’s like to be on the inside of a VC firm, here are some things I wish I had understood when I pitched myself.

  1. Be human; be yourself. Be prepared and have a pitch, but be willing to go off script. Talk about the parts of what you’re doing that are the most exciting to you! And in general, it’s probably best not to just jump into a PowerPoint deck. Take a few minutes to introduce yourself, and hear a bit from who you’re seeing. Don’t get too informal, of course – you’re still in a business context – but try to interact in as authentic a working style as you can.
  2. Seek out investors who lean forward, who engage, who ask you tough questions. Tough questions aren’t always fun, but they’re ultimately what makes your company better.
  3. You should ask questions, too, particularly to understand how the investor thinks about businesses like yours. I personally love getting questions and like a spirited debate. Helps us get to know each other.
  4. Be resilient. A “no” from a few partners or firms doesn’t mean you won’t get funded. As mentioned above, a lot of times it’s context.
  5. Be persistent. A “no” on this round doesn’t mean that an investor won’t be better, or more able to work on your company in the next round.
  6. Remember that relationships are progressions. Don’t read too much into any particular interaction. Some investors ask a bunch of questions in first meetings. Some listen more and engage more as the process goes on. Everyone is different. When in doubt about what they’re thinking, ask!
  7. Above all, don’t think of fundraising as a transaction to get finished and move onto the next thing. It is important to get the funding you need, but you’ll live with your investor for the life of your startup (and really beyond, relationship-wise). Think about it like the balancing act when you’re trying both to attract and evaluate an all-star member of your team.

Your mileage may vary, of course. But hopefully this bit of context will make the difference for you between just a pitch meeting and the start of a world-changing new relationship.

John Lilly is a partner at Greylock Partners. Prior to Greylock, John was CEO of Mozilla, makers of Firefox. In addition to leading Greylock’s investments in Tumblr, Dropbox, Clearslide and Citrus Lane, he’s also on the boards of directors of Mozilla and Code for America. Greylock is an investor in PandoDaily.